ATC Approach Bug

You are correct; in communication between pilot and controller, the altitude is in MSL.
For an airport at sea-level, the transition altitude is indeed 5000 feet MSL.

The general rule, for calculating altitude for transition we will alway need to understand that the airspace in IF has a ceiling of 5000 feet AGL, so transition altitude (in MSL) is very much depending on airport elevation. More on transition altitude here.